Reaction SMILES: IC(C)CC1CN([C@@H](CC)C(N)=O)C(=O)C1.[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:27][C:25](=O)[CH2:24][CH2:23]1.S(Cl)([Cl:30])=O.[CH3:32][OH:33]>[Cl-].[Zn+2].[Cl-]>[CH3:32][O:33][C:25](=[O:27])[CH2:24][CH2:23][CH:22]([Cl:30])[CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]
Reactant: CO
Reactant: CCCCCC1CCC(=O)O1
Reactant: O=S(Cl)Cl
Agent: CC[C@@H](C(N)=O)N1CC(CC(C)I)CC1=O
Agent: [Cl-]
Agent: [Zn+2]
Product: CCCCCC(Cl)CCC(=O)OC
Reaction time: 24 h

Procedure:
Opening of the Lactone In a three necked flask, under argon, TMSI (51 ml, Aldrich) is added to a solution of the crude 4-allyl-butyrolactone 366 (see procedure §2.1.3., 22.9 g, 0.181 mol.) cooled at 0° C. The solution is stirred for 2 h at room temperature and hydrolysed with 1N HCl (300 ml). The aqueous layer is extracted with CH2Cl2 and the combined organic phase washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the crude 3-(iodo)methyl-5-hexenoic acid 367 (44.5 g). 1H NMR (250 MHz, CDCl3): 1.80-2.05 (m, 2H), 2.20 (t, 2H), 2.40-2.60 (t, 2H), 5.10-5.20 (m, 2H), 5.15-5.80 (m, 1H). Step 2: Chlorination of the Iodo Acid In a three necked flask fitted with a reflux condenser, under argon, a solution of thionyl chloride (25.5 ml) and the crude iodo acid 367 (44.5 g, 0.175 mol.) in benzene (90 ml) is stirred for 24 h at room temperature. The solvents are evaporated under vacuo to afford the crude 3-(iodo)methyl-5-hexenoic acid chloride 368 (47 g) which is used directly in the next step without any further purification. 1H NMR (250 MHz, CDCl3): 1.90-2.05 (m, 2H), 2.15 (t, 2H), 2.90-3.10 (m, 2H), 3.25 (dd, 1H), 3.35 (dd, 1H), 5.10-5.20 (m, 2H), 5.15-5.80 (m, 1H). Step 3: Acylation-alkylation with S-2-amino-butyramide In a three necked flask, under argon, the crude acid chloride 368 (47 g, 0.172 mol.) in CH2Cl2 (300 ml) is added dropwise to a mechanically stirred suspension of molecular sieves (29 g), powdered KOH (22.3 g), anhydrous Na2SO4 (28.8 g), tetra-n-butyl ammonium bromide (2.8 g, 0.0086 mol.) and S-2-amino butyramide ([α]25D=+19.35°; 26.3 g, 0.26 mol.) in CH2Cl2 (470 ml) cooled at 0° C. The solution is stirred for 5 h at −5° C., powdered KOH is added (6.2 g) and the stirring is continued for 3 h at −5° C. The reaction mixture is filtered on hyflocel and the solvent is evaporated in vacuo. The crude reaction mixture is purified successively by chromatography on silicagel (AcOEt/i-PrOH: 97/03 (v/v)) and preparative chromatography on a chiral-stationary phase (Hexane/EtOH) to afford the two isomers of (2S)-2-(4-allyl-2-oxo-1-pyrrolidinyl)butanamide (respectively 6.0 (228) and 5.48 g (224); 16 and 15%). Two minor impurities are also isolated following the chiral chromatography, namely two stereoisomers of (2S)-2-[4-(2-iodopropyl)-2-oxo-1-pyrrolidinyl]butanamide 225 (0.22 g) and 226 (0.27 g) as white solids after recrystallisation. 2.2.2. By Alkylation/Acylation of a Butyramide The synthesis of the two stereoisomers of (2S)-2-(5-nonyl-2-oxo-1-pyrrolidinyl)butanamide is representative: Step 1: Opening of the Lactone To a solution of γ-nonalactone (0.32 ml, 2 mmol) in thionyl chloride (164 μl, 2.25 mmol), zinc chloride (12 mg, 0.088 mmol) is added at room temperature and the mixture is stirred for 24 h. Excess methanol is added and the reaction mixture is stirred for 10 min and then concentrated under reduced pressure to give 4-chloro-nonanoic acid methyl ester used as such.